Dimethylformamide → Thieno[3,2-C]pyridine-2-carbaldehyde

HRID 1362043Notes

Reaction equation

HRID 1362043 reaction equation
[S:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[CH:3]=[CH:2]1.C([Li])CCC.CCCCCC.CN([CH:24]=[O:25])C>C1COCC1>[S:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[CH:3]=[C:2]1[CH:24]=[O:25]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8058HexaneHCID 67500Thieno(3,2-c)pyridineHCID 178418339Butyllithium

Product 1

HCID 20440932Thieno[3,2-C]pyridine-2-carbaldehydeYield 41.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of thieno[3,2-c]pyridine (500 mg, 3.70 mmol) in anhydrous THF (10 mL) was stirred under argon and maintained at −78° C. while a solution of 1.6 M n-butyllithium in hexane (2.5 mL, 4.07 mmol) was added dropwise. The resulting wine red solution was stirred for 5 min. then DMF (573 μL, 7.4 mmol) was added. The cooling bath was removed and the reaction mixture was stirred at room temperature for 16 hr. The reaction mixture was treated with 10% aqueous HCl, made alkaline with saturated aqueous NaHCO3 and extracted with CH2Cl2 (2×50 mL) The combined organic fractions were concentrated in vacuo to give an oily residue which was subjected to flash chromatography on silica gel (70% ethyl acetate:hexanes) to give the title compound as a white solid (41.5%): 1H-NMR (300 MHz, DMSO-d6) δ 10.20 (s, 1H), 9.39 (s, 1H), 8.60 (s, 1H), 8.59 (d, J=5.5 Hz, 1H), 8.19 (d, J=5.6 Hz, 1H); MS (ES) m/e 164 (M+H)+.

Workup

  1. additionwas added dropwise
  2. customThe cooling bath was removed
  3. stirringthe reaction mixture was stirred at room temperature for 16 hr
  4. additionThe reaction mixture was treated with 10% aqueous HCl
  5. extractionextracted with CH2Cl2 (2×50 mL) The combined organic fractions
  6. concentrationwere concentrated in vacuo
  7. customto give an oily residue which

Sources & evidence

ORD record
ord-f79bba99bb02476abb71ad7c6923d46a
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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